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Synthesis and Reactions of Triptycene‐Derived Bromocalix[5]arenes: Conformational Transformation from Cone to 1,2‐Alternate
Author(s) -
Xia YuXiang,
Han Ying,
Chen ChuanFeng
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301668
Subject(s) - triptycene , chemistry , dichloromethane , moiety , bromine , calixarene , stereochemistry , polymer chemistry , organic chemistry , molecule , solvent
Triptycene‐derived p ‐dibromocalix[5]arene was synthesized by a fragment‐coupling approach, whereas treatment of the triptycene‐derived calix[5]arene containing three p ‐ tert ‐butyl phenol groups and a 1,8‐dimethoxytriptycene moiety with excess bromine in dichloromethane at room temperature produced triptycene‐derived p ‐pentabromocalix[5]arene directly. Methyl etherification and Suzuki coupling reactions were then carried out. As a result, a series of triptycene‐derived calix[5]arene derivatives in fixed cone and 1,2‐alternate conformations were obtained. Moreover, conformation transformations of triptycene‐derived calix[5]arenes from cone to 1,2‐alternate forms could also be achieved.